Date published: 2025-12-5

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Secologanin (CAS 19351-63-4)

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Alternate Names:
LONICEROSIDE
Application:
Secologanin is a useful analytical standard
CAS Number:
19351-63-4
Purity:
≥88%
Molecular Weight:
388.37
Molecular Formula:
C17H24O10
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Secologanin is a pivotal terpenoid glycoside that plays a critical role in the biosynthesis of indole alkaloids, a diverse class of compounds widely studied for their intricate structures and biological activities. Secologanin is integral to the metabolic pathways that lead to the formation of various molecules, such as vincristine and vinblastine, which are noted for their roles in research related to cell cycle dynamics and cellular communication. The compound′s involvement in the synthesis of these molecules provides a foundational understanding of plant secondary metabolism and the ecological interactions mediated by these chemical entities. By acting as a key precursor in the enzymatic processes that generate complex alkaloids, secologanin not only contributes to the diversification of natural products but also facilitates the exploration of their synthesis, offering insights into the development of bio-inspired synthesis strategies.


Secologanin (CAS 19351-63-4) References

  1. Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase.  |  Irmler, S., et al. 2000. Plant J. 24: 797-804. PMID: 11135113
  2. Biotransformation of tryptamine and secologanin into plant terpenoid indole alkaloids by transgenic yeast.  |  Geerlings, A., et al. 2001. Appl Microbiol Biotechnol. 56: 420-4. PMID: 11549013
  3. Investigation of Pictet-Spengler type reactions of secologanin with histamine and its benzyl derivative.  |  Beke, G., et al. 2002. J Nat Prod. 65: 649-55. PMID: 12027735
  4. Comparison of extraction methods for secologanin and the quantitative analysis of secologanin from Symphoricarpos albus using 1H-NMR.  |  Kim, HK., et al. 2004. Phytochem Anal. 15: 257-61. PMID: 15311846
  5. [Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites].  |  Inoue, K. 2005. Yakugaku Zasshi. 125: 31-49. PMID: 15635280
  6. [Molecular mechanisms and chemotaxonomy in the indole alkaloids derived from secologanin. (One drop in the sea, the sea in one drop)].  |  Szabó, FL. 2006. Acta Pharm Hung. 76: 67-80. PMID: 17094665
  7. A new type of monoterpenoid indole alkaloid precursor from Alstonia rostrata.  |  Cai, XH., et al. 2011. Org Lett. 13: 3568-71. PMID: 21688858
  8. A 7-deoxyloganetic acid glucosyltransferase contributes a key step in secologanin biosynthesis in Madagascar periwinkle.  |  Asada, K., et al. 2013. Plant Cell. 25: 4123-34. PMID: 24104568
  9. Inter-organ transport of secologanin allows assembly of monoterpenoid indole alkaloids in a Catharanthus roseus mutant.  |  Kidd, T., et al. 2019. Phytochemistry. 159: 119-126. PMID: 30611871
  10. Tabernabovines A-C: Three Monoterpenoid Indole Alkaloids from the Leaves of Tabernaemontana bovina.  |  Yu, Y., et al. 2019. Org Lett. 21: 5938-5942. PMID: 31294995
  11. Privileged Biorenewable Secologanin-Based Diversity-Oriented Synthesis for Pseudo-Natural Alkaloids: Uncovering Novel Neuroprotective and Antimalarial Frameworks.  |  Zhu, H., et al. 2021. ChemSusChem. 14: 5320-5327. PMID: 34636473
  12. Single mutations toggle the substrate selectivity of multifunctional Camptotheca secologanic acid synthases.  |  Miller, JC. and Schuler, MA. 2022. J Biol Chem. 298: 102237. PMID: 35809640
  13. The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharanthus roseus cell culture.  |  Contin, A., et al. 1998. FEBS Lett. 434: 413-6. PMID: 9742965

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Secologanin, 5 mg

sc-229289
5 mg
$132.00